N7-(1-hydroxy-3-buten-2-yl)guanine | 89315-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N7-(1-hydroxy-3-buten-2-yl)guanine
• 英文别名: EB-GII；2-Amino-7-(1-hydroxybut-3-en-2-yl)-1H-purin-6(7H)-one；2-amino-7-(1-hydroxybut-3-en-2-yl)-1H-purin-6-one
• CAS: 89315-24-2
• 化学式: C₉H₁₁N₅O₂
• 分子量: 221.219
• InChiKey: JVLXVOQCSGQHDB-UHFFFAOYSA-N

物化性质

• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环氧丁烯 、 鸟嘌呤 在 Tris-HCl buffer 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 N7-(1-hydroxy-3-buten-2-yl)guanine 、 N7-(2-hydroxy-3-buten-1-yl)guanine
  参考文献：
  名称：

  丁二烯的高分子加合物。

  摘要：

  丁二烯（BD）是一种重要的工业化学品，被归类为可能的人类致癌物。观察到对BD致癌作用的敏感性存在明显的物种差异，这可能是由于其代谢差异造成的。在这项工作中，由BD的反应性代谢产物形成的鸟嘌呤和腺嘌呤加合物被分离出来，并通过紫外光谱，液体二次离子质谱和串联质谱，电喷雾质谱和核磁共振谱进行结构表征。通过使嘌呤核苷碱基或核苷与环氧丁烯（EB）或二环氧丁烷（DEB）反应，然后进行HPLC分离来制备加合物。鸟嘌呤（Gua）与EB的反应产生了两种异构产物，N7-（2-羟基-3-丁烯-1-基）鸟嘌呤（EB-Gua I）和N7-（1-羟基-3-丁烯-2-基）鸟嘌呤（EB-Gua II）。腺嘌呤在N3处的反应导致形成N3-（2-羟基-3-丁烯-1-基）腺嘌呤（EB-Ade I）和N3-（1-羟基-3-丁烯-2-基）（ EB-Ade II）。DEB的主要鸟嘌呤加合物被鉴定为N7-（2'，3'，4'-三羟丁基）

  DOI：

  10.1016/0300-483x(96)03429-4

文献信息

• NanoLC/ESI⁺ HRMS³ Quantitation of DNA Adducts Induced by 1,3-Butadiene
  作者：Dewakar Sangaraju、Peter W. Villalta、Susith Wickramaratne、James Swenberg、Natalia Tretyakova

  DOI：10.1007/s13361-014-0916-x

  日期：2014.7.1

  Human exposure to 1,3-butadiene (BD) present in automobile exhaust, cigarette smoke, and forest fires is of great concern because of its potent carcinogenicity. The adverse health effects of BD are mediated by its epoxide metabolites such as 3,4-epoxy-1-butene (EB), which covalently modify genomic DNA to form promutagenic nucleobase adducts. Because of their direct role in cancer, BD-DNA adducts can be used as mechanism-based biomarkers of BD exposure. In the present work, a mass spectrometry-based methodology was developed for accurate, sensitive, and precise quantification of EB-induced N-7-(1-hydroxy-3-buten-2-yl) guanine (EB-GII) DNA adducts in vivo. In our approach, EB-GII adducts are selectively released from DNA backbone by neutral thermal hydrolysis, followed by ultrafiltration, offline HPLC purification, and isotope dilution nanoLC/ESI+-HRMS3 analysis on an Orbitrap Velos mass spectrometer. Following method validation, EB-GII lesions were quantified in human fibrosarcoma (HT1080) cells treated with micromolar concentrations of EB and in liver tissues of rats exposed to sub-ppm concentrations of BD (0.5–1.5 ppm). EB-GII concentrations increased linearly from 1.15 ± 0.23 to 10.11 ± 0.45 adducts per 106 nucleotides in HT1080 cells treated with 0.5–10 μM DEB. EB-GII concentrations in DNA of laboratory rats exposed to 0.5, 1.0, and 1.5 ppm BD were 0.17 ± 0.05, 0.33 ± 0.08, and 0.50 ± 0.04 adducts per 106 nucleotides, respectively. We also used the new method to determine the in vivo half-life of EB-GII adducts in rat liver DNA (2.20 ± 0.12 d) and to detect EB-GII in human blood DNA. To our knowledge, this is the first application of nanoLC/ESI+-HRMS3 Orbitrap methodology to quantitative analysis of DNA adducts in vivo.

  ± 0.05)天。
• Macromolecular adducts of butadiene
  作者：Natalia Yu. Tretyakova、Yu-pang Lin、Patricia B. Upton、Ramiah Sangaiah、James A. Swenberg

  DOI：10.1016/0300-483x(96)03429-4

  日期：1996.10

  spectrometry and nuclear magnetic resonance spectroscopy. The adducts were prepared by reacting purine nucleobases or nucleosides with epoxybutene (EB) or diepoxybutane (DEB) followed by HPLC separation. The reaction of guanine (Gua) with EB resulted in two isomeric products, N7-(2-hydroxy-3-buten-1-yl)guanine (EB-Gua I) and N7-(1-hydroxy-3-buten-2-yl)guanine (EB-Gua II). The reaction of adenine at N3

  丁二烯（BD）是一种重要的工业化学品，被归类为可能的人类致癌物。观察到对BD致癌作用的敏感性存在明显的物种差异，这可能是由于其代谢差异造成的。在这项工作中，由BD的反应性代谢产物形成的鸟嘌呤和腺嘌呤加合物被分离出来，并通过紫外光谱，液体二次离子质谱和串联质谱，电喷雾质谱和核磁共振谱进行结构表征。通过使嘌呤核苷碱基或核苷与环氧丁烯（EB）或二环氧丁烷（DEB）反应，然后进行HPLC分离来制备加合物。鸟嘌呤（Gua）与EB的反应产生了两种异构产物，N7-（2-羟基-3-丁烯-1-基）鸟嘌呤（EB-Gua I）和N7-（1-羟基-3-丁烯-2-基）鸟嘌呤（EB-Gua II）。腺嘌呤在N3处的反应导致形成N3-（2-羟基-3-丁烯-1-基）腺嘌呤（EB-Ade I）和N3-（1-羟基-3-丁烯-2-基）（ EB-Ade II）。DEB的主要鸟嘌呤加合物被鉴定为N7-（2'，3'，4'-三羟丁基）